
Vacation rentals with a pool in Highland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Highland
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Gorgeous Resort Style Mountain view Pool Villa
Gorgeous 3 bed/2 bath single floor home with PRIVATE Heated POOL that feels like a 5 Star resort with FREE EV charging for your car. Beautiful backyard, BBQ grill and 12 seater lounge, pool & hot tub with water slide. Fireplace, 85” OLED TV, work space, High speed Wi-Fi , Gym. Fully equipped kitchen, 6-burner gas range stove, rice cooker, coffeemaker etc. Laundry room with washer/dryer, iron/board, air conditioning, heating, linens/towels, Pack & play. Digital door lock, Driveway for 4 vehicles.

Oasis in the canyon
This charming guest house is well lit located on a quiet neighborhood easy access from two mayor interstates and shopping a 15 min drive to Redlands and 7 min to Loma Linda hospital what ever the reason of your stay if you want peace and quiet and a fun place to enjoy the cool evenings this is it. Don’t forget the pool to relax during hot days of summer we have a piece of tropical paradise on our backyard also we are at the guest request only 30 feet and a knock on our back door! WE HAVE DOGS!

Feet Away From Slopes Modern Snow Summit Cabin
Experience the best of Big Bear with this remodeled townhouse, only a two-minute walk from the top snowboarding destination in town! Located adjacent to Snow Summit Ski Resort, you can enjoy skiing/snowboarding in the winter and mountain biking once summer arrives. Fantastic amenities including private parking, air conditioning, a rare gem in Big Bear. Community amenities, such as barbecue area, sauna and a seasonal pool to make your stay more enjoyable. The ultimate ski and ski out experience.

Quaint Farmhouse Getaway - Entire Place (Condo)
Enjoy your stay at this farmhouse style 2 bed 2 bath condo! Extremely clean and well maintained, this space is conveniently located a few minutes from the downtown area, Central Plaza, and walking distance from Riverside's well known Mt. Rubidoux Hike; a 1-mile trek that gives a stunning view of the entire city. There is a park across the street that kids love which also has a nice walking path. The neighborhood is very quiet and peaceful. Access to Wifi, washer/dryer, 2 car garage, and more!

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!
Located in beautiful South Redlands near Prospect Park, this detached cottage has its own private and inviting fenced backyard, nicely landscaped with comfortable patio furniture. Inside you will find separate living and bedroom spaces, charming decor, Heating/A/C, Cable TV, WIFI, kitchenette with microwave, Keurig coffee maker and compact refrigerator, fine linens, comfortable queen sized bed, and newer bathroom. Conveniently located near Downtown Redlands, University of Redlands and ESRI!

Peaceful Private Retreat In The Heart Of Town
Meticulously designer-renovated modern home “The Nest “is surrounded by mature tree and nestled beneath the mountains in South Redlands. Whether you’re looking to spend time with loved ones, vacationing or work remotely in a peaceful environment, this is the place to do it all. Relax by the fireplace while light pours in from the wall of windows, with pleasant sparkling pool, grill and chill on the backyard, and explore nature right outside your front door. Conveniently located in Redlands!

All-in-One Pool Guest House w Private Backyard!
We’d love to host you at our cozy and fully equipped guest house—perfect for families and friends! Located in a quiet, premiere gated community, just 6 min off the 60 fwy. You'll have the guest house all to yourself!This private guest house has its own entrance, pool, and private backyard, offering 600+ sqft of space, including a studio layout, 1 bathroom, and all the essentials you need for a comfortable stay. We can accommodate up to 4 guests and always do our best to meet your needs!

The Blue Cabin
Relax at this unique, tranquil, and comfortable mini home in our backyard. Surrounded by a beautiful garden with a wide variety of succulents and a relaxing pool. With a space to enjoy reading or listening to music. Equipped with microwave, Keurig coffee machine, mini refrigerator, toaster, blender, washer/dryer, and tableware. The mini home has air conditioning and heating system for comfort and a smart TV. No parties allowed.(SPACE EQUIPPED ONLY FOR 2-3 PEOPLE *no more than 3 fit*)

Hot Tub, Fire Pit/Game Room/ Near NOS Center
Welcome to our meticulously clean three-bedroom, two-bath haven in San Bernardino! This gorgeous house is designed for comfort and entertainment. Unwind in the game room with a pool table or gather around the patio's fire pit. Experience the charm of our outdoor space, featuring a second fire pit in the grass area. Create lasting memories surrounded by freshly painted murals near the inviting pool and brand-new Jacuzzi – perfect for starlit evenings with friends and family.

Riverside Serenity Spring Oasis|Spa/Pool/Mini Golf
Welcome to our exquisite Riverside retreat, where luxury meets family fun! Here's what makes our place truly special: 🔥 Cozy Fireplace for Chilly Evenings 🌴 Tropical Oasis with a Sparkling Pool 🌟 Jacuzzi Bliss under the Stars ⛳ Mini Golf Extravaganza. 🏡 Spacious and Clean Rooms 📍 Centrally Located Convenience: Downtown Riverside, UCR, NOS Center, 210 Freeway, Yaamava, and local shops *~Fun-Filled Family Environment!~* Book now!

Dreamy Escape Private Entrance /pool/near Yaamava
Our location is close to dining, hiking, shopping, movie theaters, and popular attractions like the National Orange Show Event Center (NOS), Yaamava Resort & Casino, vibrant nightlife, Redlands University, and Loma Linda University. You'll love our place for its location, inviting ambiance, outdoor space, and friendly neighborhood. It's the perfect spot for couples, solo adventurers, and business travelers looking for a cozy getaway!

Lakefront Walk 2 Village w/ Dock Access & Pets
Experience the breathtaking winter scenery of Big Bear Lake from the luxury of your room at Lakefront at the Village. This 2 bedroom 2 bath home is located at Forest Shores with its own private boat dock (subject to availability) Everything is within a short 5 minute walk at this gorgeous updated retreat. Did we mention it's lakefront? Dock is seasonal and subject to change in the winter.
Popular amenities for Highland rentals with a pool
House rentals with a pool

Spacious Pool | Hot Tub | Pool Table | BBQ Grill | Basketball

Pool Home w/ Game Room near NOS Center

Perfect home for large groups! Newly remodeled

Modernized condo in the Arrowhead Village with spa

Valley of Guadalupe Escape gem

So. Cal. Living near Redlands-Beautiful 3,000+Home

Scenic views pool/spa/bbq/karaoke/games No Parties

SoCal’s Pet Friendly Luxury Family Pool spa Resort
Condo rentals with a pool

The Cozy Cottage Condo - Jacuzzi/3mi to slopes

Amazing New Condo (Victoria Garden/Ontario Mills)

Big Bear 2BR Condo on Beautiful Resort

The best memories are made here.

Lakeview Getaway | Game Rm, Pool, Spa, Sauna!

1BedrmCondo-Kitchen-WiFi-2Bathrms-King+Sofabed GSL

Lakeside Lumberjack Lodge - Condo *Pool/Jacuzzi*

Casita Condo | Jacuzzi | 3mi to slopes
Other vacation rentals with a pool

Luxury 3bd 3b Oak Glen Pool Resort Panoramic Views

Modern Studio Near LLU Hospital

Modern Riverside Pool Home| Pet Friendly |CBU, UCR

Authentic Mexican Casita, Pool, Spa, Fire, WIFI

Cozy Lakefront Retreat w/ Views & Fireplace

Two Trees Tiny House

Golden - 1bd Condo

Luxurious, Private 1 Bedroom Guest House with Pool
When is the best time to visit Highland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 76 | € 90 | € 91 | € 101 | € 91 | € 101 | € 96 | € 94 | € 93 | € 94 | € 91 | € 79 |
| Avg. temp | 14°C | 14°C | 15°C | 16°C | 18°C | 20°C | 23°C | 24°C | 24°C | 21°C | 17°C | 14°C |
Quick stats about vacation rentals with a pool in Highland

Total vacation rentals
Explore 20 vacation rentals in Highland

Nightly prices starting at
Highland vacation rentals start at € 35 per night before taxes and fees

Verified guest reviews
Over 1,320 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Highland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Highland rentals

4.9 Average rating
Highland stays are highly rated by guests—averaging 4.9 out of 5!
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- Disneyland Park
- Knott’S Berry Farm
- Big Bear Mountain Resort
- Bear Mountain Ski Resort
- Anaheim Convention Center
- Snow Summit
- Disney California Adventure Park
- Palm Springs Convention Center
- Pechanga Resort Casino
- Mountain High
- Honda Center
- National Orange Show Events Center
- Angel Stadium of Anaheim
- Palm Springs Aerial Tramway
- Disneyland Resort
- Indian Canyons
- Alpine Slide at Magic Mountain
- Tahquitz Creek Golf Resort
- Snow Valley Mountain Resort
- Glen Ivy Hot Springs Spa
- Big Bear Alpine Zoo
- Chino Hills State Park
- Whitewater Preserve
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